反応 #2358583

反応方程式

3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde

tert-butyl N-[2-(methylamino)ethyl]carbamate

NaBH(OAc)3

→

tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)carbamate

収率 83.5%

溶媒

dichloroethane

反応条件

後処理

1. 1
   その他The reaction was quenched with 50 mL of saturated aqueous sodium bicarbonate solution
2. 2
   抽出The resulting mixture was extracted with 3×200 mL of dichloromethane
3. 3
   乾燥The combined organic layers was dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated under vacuum
5. 5
   その他The residue was purified on a silica gel column
6. 6
   洗浄eluted with 30-100% ethyl acetate in petroleum ether

実験手順

A mixture of 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde (3.2 g, 10.45 mmol, 1.00 equiv), tert-butyl N-[2-(methylamino)ethyl]carbamate (2.2 g, 12.63 mmol, 1.21 equiv) and NaBH(OAc)3 (6.65 g, 31.38 mmol, 3.00 equiv) in dichloroethane (30 mL) was stirred for 2 h at room temperature. The reaction was quenched with 50 mL of saturated aqueous sodium bicarbonate solution. The resulting mixture was extracted with 3×200 mL of dichloromethane. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 30-100% ethyl acetate in petroleum ether to give 4.05 g (83%) of tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)carbamate as a light yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.48 (s, 1H), 5.35-5.30 (m, 1H), 4.13-4.03 (m, 1H), 3.71-3.63 (m, 1H), 3.36 (s, 2H), 3.26-3.25 (m, 2H), 2.52-2.49 (m, 2H), 2.21 (s, 3H), 2.09-2.01 (m, 3H), 1.68-1.58 (m, 3H), 1.44 (s, 9H) ppm. LCMS (method C, ESI): RT=0.58 min, m/z=465.0 [M+H]+.

出典